EP1248104A2 - MBTH für die Messung von aliphatischen Aldehyden - Google Patents

MBTH für die Messung von aliphatischen Aldehyden Download PDF

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Publication number
EP1248104A2
EP1248104A2 EP02251865A EP02251865A EP1248104A2 EP 1248104 A2 EP1248104 A2 EP 1248104A2 EP 02251865 A EP02251865 A EP 02251865A EP 02251865 A EP02251865 A EP 02251865A EP 1248104 A2 EP1248104 A2 EP 1248104A2
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EP
European Patent Office
Prior art keywords
aldehyde
mbth
measuring device
test sample
oxidant
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP02251865A
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English (en)
French (fr)
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EP1248104A3 (de
Inventor
Szu-Min Lin
Peter Zhu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ethicon Inc
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Ethicon Inc
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Publication date
Application filed by Ethicon Inc filed Critical Ethicon Inc
Publication of EP1248104A2 publication Critical patent/EP1248104A2/de
Publication of EP1248104A3 publication Critical patent/EP1248104A3/de
Ceased legal-status Critical Current

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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N31/00—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods
    • G01N31/22—Investigating or analysing non-biological materials by the use of the chemical methods specified in the subgroup; Apparatus specially adapted for such methods using chemical indicators
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/20—Oxygen containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/20—Oxygen containing
    • Y10T436/200833—Carbonyl, ether, aldehyde or ketone containing

Definitions

  • the field of the invention relates to a method to detect a point of interest (POI) of an aldehyde in a test sample such as a disinfectant.
  • a device or test strip are used to detect the point of interest of the aldehyde in the test sample.
  • MBTH (3-methyl-2-benzothiazolinone hydrazone hydrochloride) is a well-known aldehyde analysis reagent. Using this reagent, an azine is formed between an aldehyde and MBTH. MBTH is also oxidized by an oxidizing agent such as ferric chloride to another species, which combines with the azine to form a blue colored formazan structure.
  • This reaction was originally described by Sawicki et al. (Sawicki et al. (1961) Analytical Chemistry vol. 33 (1): 93-96) as an extremely sensitive assay for detection of aldehydes in exhaust fumes. The method of Sawicki et al. was subsequently modified to achieve even higher sensitivity to allow detection of aldehydes in air in the parts-per-billion range (Hauser et al. (1964) Analytical Chemistry vol. 36 (3): 679-681).
  • EP 0 016 578 teaches application of the reaction of MBTH with aldehydes to aqueous samples.
  • the assay was useful with samples in the parts per million range.
  • the MBTH procedure was also adapted for use in seawater samples to measure the formaldehyde given off by the marine methanotroph, Methylomonas pelagica (Eberhardt et al. (1985) Marine Chemistry vol. 17: 199-212). This method has proven very useful in analysis of dilute aldehyde-containing samples. However, for concentrated aldehyde analysis, this method is inconvenient due to the need for dilutions. A new method is proposed here for use of the MBTH procedure with samples which contain higher concentrations of aldehydes such as disinfectants.
  • the present invention pertains to a method of determining the presence of a point of interest of an aldehyde in a test sample comprising the steps of:
  • the color in the test sample is blue, green, yellow or any combination thereof.
  • the oxidant is selected from the group including ferric chloride, potassium ferricyanide, lead tetraacetate and periodic acid. In a most preferred embodiment, the oxidant is ferric chloride.
  • the aldehyde is glutaraldehyde.
  • the oxidant is mixed with the test sample at the same time as the MBTH reacts with the aldehyde. In an alternate preferred embodiment, the oxidant is added to the test sample after the MBTH reacts with the aldehyde.
  • the method further includes drawing up a fixed volume of an aldehyde-containing test sample before or during the reaction of aldehyde with MBTH.
  • the method includes loading the fixed volume to a measuring device having a gas or vapor permeable but liquid impermeable membrane.
  • the method includes loading the fixed volume to a measuring device containing the MBTH or FeCl 3 .
  • the aldehyde in the test sample is applied to an absorbent material.
  • the absorbent material is a nylon membrane.
  • the absorbent material contains MBTH or FeCl 3 .
  • the present invention also pertains to a liquid measuring device including at least one compartment for determining the presence of a point of interest of an aldehyde in a test sample including a first compartment having a proximal and distal end which contains an amount of MBTH that reacts with a aldehyde in a first reacting step, wherein said amount is sufficient to react with the aldehyde to the point of interest.
  • the first compartment further includes an oxidant that reacts with the MBTH.
  • the liquid measuring device further includes a second compartment in liquid communication with the first compartment by means of a valve.
  • the second compartment contains an oxidant that reacts with the MBTH.
  • the liquid measuring device is a syringe or pipet.
  • the liquid measuring device further includes a gas or vapor permeable but liquid impermeable membrane between the proximal and distal end of the first compartment.
  • the liquid measuring device may also include a filter at or near the distal end of the first compartment.
  • the liquid measuring device further includes a valve at or near the distal end of the first compartment.
  • the liquid measuring device further includes a needle assembly.
  • the aldehyde in the test sample is selected from the group consisting of glutaraldehyde and formaldehyde.
  • the present invention also pertains to a test strip including at least one absorbent material for determining the presence of a point of interest of an aldehyde in a test sample including a first absorbent material which contains an amount of MBTH that reacts with an aldehyde in a first reacting step, wherein the amount is sufficient to react with the aldehyde to the point of interest.
  • the first absorbent material of the test strip further includes an oxidant that reacts with the MBTH.
  • the test strip further includes a second absorbent material containing an oxidant that reacts with the MBTH.
  • the second absorbent material is separated from the first absorbent material with a separator.
  • the separator includes a removable liquid impermeable film or a blank absorbent material.
  • the test strip further includes an aldehyde tester.
  • the aldehyde tester is a Shiff's reagent.
  • the test strip further includes a pH tester.
  • the pH tester includes a pH dye indicator selected from the group including bromothymol blue, brilliant yellow, neutral red, rosolic acid, phenol red, 3-nitrophenol, orange II, phenolphthalein, o-cresolphthalein, nile blue A and thymolphthalein.
  • the test strip further includes at least one color comparator.
  • Figure 1 shows the MBTH-glutaraldehyde color reaction principle.
  • MBTH combines with an aldehyde to form a colorless azine ( A ) and MBTH is oxidized to a species ( B ).
  • B a species
  • Intermediate A and B react to form ( C ), a formazan.
  • Figure 2 shows a pipette and two variants of a syringe with a gas or vapor permeable liquid impermeable barrier.
  • Figure 3A shows the coupling of the gas or vapor permeable liquid impermeable barrier to the syringe or pipette.
  • Figure 3B illustrates how inserts 4 at the top of the pipette or syringe attach the gas or vapor permeable liquid impermeable barrier to the pipette or syringe.
  • Figure 3C illustrates a holder 5 that holds the inserts in place.
  • Figure 3D shows the inserts and the coupling of the gas or vapor permeable liquid impermeable barrier.
  • Figure 4 is an expanded view of figure 3C which shows a gas or vapor permeable liquid impermeable barrier 1, an insert 4, and a holder 5.
  • Figure 5 shows one embodiment of the invention where the position of the gas or vapor permeable liquid impermeable membrane is adjusted by means of a screw.
  • Figures 6A and 6B show embodiments of the liquid delivery apparatus with all chemicals in one chamber.
  • Figure 6C shows a two chambered embodiment of the liquid delivery apparatus.
  • the test sample may be taken into the first chamber for reaction with the first compound such as MBTH in Figure 1. Then the sample is moved by means of a one-way valve or a manual ON/OFF valve 8 into the second chamber where the test sample reacts with the second compound such as FeCl 3 of Figure 1.
  • Figure 7A shows a two-layered nylon membrane where the bottom layer comprises FeCl 3 , the top layer comprises MBTH and the two layers are separated by a liquid impermeable film.
  • Figures 7B and 7C show the nylon membrane after application of glutaraldehyde at an earlier stage ( Figure 7B) and a later stage (Figure 7C).
  • Figure 8A shows a three layered nylon membrane where the bottom layer comprises FeCl 3 , the top layer comprises MBTH and the two layers are separated by a blank nylon membrane.
  • Figures 8B and 8C show the nylon membrane after application of glutaraldehyde at an earlier stage ( Figure 8B) and a later stage (Figure 8C).
  • Figures 9 A-E show 5 variations of a tester strip.
  • Figure 9A shows a tester strip with an aldehyde indicator 11.
  • Figure 9B shows a tester strip with an aldehyde indicator 11 and an aldehyde tester 12.
  • Figure 9C shows a tester strip with an aldehyde indicator 11 and a pH tester 13.
  • Figure 9D shows a tester strip with an aldehyde indicator 11, an aldehyde tester 12, and a pH tester 13.
  • Figure 9E shows a tester strip with an aldehyde indicator 11, an aldehyde tester 12, a pH tester 13, and color comparators 14, 15, 16.
  • MBTH Using MBTH, an azine is formed between an aldehyde and MBTH.
  • MBTH is also oxidized by an oxidizing agent such as ferric chloride to another species B , which combines with an azine A to form a blue colored formazan structure C .
  • an oxidizing agent such as ferric chloride
  • the MBTH reacts with the aldehyde to form an azine A . Only if there is remaining MBTH, will the MBTH be oxidized to another species, B , which combines with the azine A to form formazan C . However, if there is enough aldehyde, all of the MBTH will be converted to an azine A , the oxidant will have nothing to react with so formazan C will not be formed and there will be no blue color.
  • MBTH is the limiting reagent.
  • the amount of MBTH is just enough to neutralize the aldehyde at the point of interest.
  • MBTH is the preferred embodiment, other hydrazones may also be used such as salicylalhydrazone and p-nitrobenzalhydrazone.
  • other reagents may be used as the oxidizing agents including ferric chloride, potassium ferricyanide, lead tetraacetate, and periodic acid. In a most preferred embodiment, ferric chloride is used as the oxidizing agent.
  • the order in which the chemicals are added is important for the final color observed. For example, if MBTH is added first and ferric chloride is added last, then the final color of the solution will be light yellow when the concentration of glutaraldehyde is equal to or above the POI and will be blue when the glutaraldehyde concentration is below the POI. On the other hand, if ferric chloride and MBTH are mixed first, the final color of the solution after adding the aldehyde will vary from light green to green/ blue depending upon the amount of aldehyde in the test sample. In this case, a meter or color comparator may be needed to determine the amount of the aldehyde compared to the POI.
  • liquid-measuring device such as a pipette or syringe, for carrying out the assay.
  • This device could be used for any "fixed-volume” measurement and transfer in chemistry, biochemistry, clinical chemistry or other industries.
  • the apparatus may be a syringe or pipette with one or more barrels and plungers and a membrane barrier with or without a coupling device.
  • the membrane barrier is a gas or vapor permeable and liquid impermeable barrier. In the presence of certain pressure differences between the two sides of the barrier, the gas or vapor flows through the membrane but not the liquid.
  • Any suitable gas or vapor permeable and liquid impermeable materials can be used for this purpose. Some examples include, but are not limited to, nonwoven polyolefin, such as TyvekTM (non-woven polyethylene), or CSR (non-woven polypropylene central supply room), wrapping material and any other hydrophobic filtering materials.
  • the device contains an insert and a holder.
  • the syringe or pipette apparatus may also contain valves to control the flow of liquid.
  • the membrane barrier can be thermally bound to the syringe or pipet. It can also be attached to the syringe or pipet with an adhesive or connected to the syringe barrel by a coupling device.
  • the coupling device may be connected to an insert for altering the position of the membrane barrier. The position of the membrane barrier can be adjusted by the length of the insert.
  • the insert may be secured with a holder.
  • the membrane barrier is a gas or vapor permeable but liquid impermeable barrier.
  • the membrane barrier is positioned such that the liquid can only be filled up to the barrier.
  • the invention has several preferred embodiments.
  • a gas or vapor permeable liquid impermeable membrane 1 is fixed into the pipette 7 or syringe 6 and held in place at the desired maximum volume by means known in the art.
  • the syringe includes a plunger 3.
  • the syringe can have a metal or plastic needle with or without a needle cap.
  • a coupling device 2 is used which is larger or smaller than the diameter of the pipette 7 or syringe 6. Two parts of the pipet or syringe with different lengths can be joined together with such a coupling device.
  • FIGS 3A, 3B, 3C, 3D and Figure 4 Coupling of the membrane barrier to the syringe or pipette is shown in Figures 3A, 3B, 3C, 3D and Figure 4.
  • the membrane can be inserted into the syringe or pipet from the top of the pipette or syringe by an insert 4 which may be secured with a holder 5 and its position varied by any means known in the art such as by a screw ( Figure 5) or a slidable adjustment (Figure 4).
  • Figure 3D shows an insert which has a larger diameter than the pipette or syringe.
  • Figures 6A, 6B and 6C illustrate the use of the measuring device with this invention.
  • Figures 6A and 6B show a syringe with a gas or vapor permeable liquid impermeable barrier and two chemicals.
  • the liquid can be filled in the syringe by inserting the plastic needle into the sample solution, pulling the plunger to create a negative pressure in the syringe, and loading the liquid into the syringe.
  • the measuring device can have a filtering material (Figure 6A) or valve ( Figure 6B) to retain the chemicals in the barrel.
  • the chemical in the syringe can be in either a liquid or solid form.
  • the valve can be a one-way valve or a manual ON/OFF valve.
  • Figure 6C provides another embodiment for mixing more than one reactant successively. It has two chambers 9, 10. A fixed volume of any solution including, but not limited to an aldehyde is drawn up through a one-way valve or an ON/OFF valve 8 into the first chamber 9 where it mixes with the first reactant, for example MBTH. After a predetermined time, the reactants flow through a second one-way valve or an ON/OFF valve 8 into a second reaction chamber 10 which might contain an oxidant such as FeCl 3 , for example, to complete the reaction. Alternatively, a three-way valve can be used instead of two one-way valves.
  • Example 1 was repeated. However, no FeCl 3 was added. The solution remained milky with no blue color.
  • Example 1 was repeated. However, no glutaraldehyde was added. The solution appeared light yellow after the addition of FeCl 3 (FeCl 3 color).
  • Green/ Blue color instead of blue color formed in this case due to the addition of MBTH first, FeCl 3 second and aldehyde last.
  • Example 1 The procedure in Example 1 was repeated except different amounts of aldehyde were added (see Table 1 ).
  • the MBTH (0.1% in water) was added first, Cidex (1.75%) was added second and FeCl 3 (2.5%) was added third.
  • Exp # MBTH (1st add) Cidex (1.75%) FeCl 3 (2.5%) Observation 1 1000 ⁇ L 60 ⁇ L, no wait 100 ⁇ L, fresh All samples turned blue quickly ( ⁇ 10"). Blue color darkness of 3>2>1 was observed. 2 1000 ⁇ L 40 ⁇ L, no wait 100 ⁇ L, fresh 3 1000 ⁇ L 20 ⁇ L, no wait 100 ⁇ L, fresh
  • MBTH is not always sufficient, it reacts with aldehyde first to form an azine. Only if there is remaining MBTH, it is oxidized to another species which combines with the azine to form formazan. However, if there is enough aldehyde, all the MBTH is converted to azine and an oxidant could not get anything to react with so formazan was not formed (no blue color). Thus, by using the limiting agent MBTH to test the amount of aldehyde around the point of interest, less aldehyde would produce more blue color and more aldehyde would give less blue! This method is especially useful in the quality control of aldehyde products where a quick assay can be conducted without tedious dilutions.
  • a solution containing 1% MBTH and 1% FeCl 3 was prepared fresh using MeOH as the solvent. Nylon membranes are soaked in this solution briefly and air-dried. Cidex glutaraldehyde was dropped on the nylon membrane containing both MBTH and FeCl 3 (Table 3). Alternatively, other absorbent hydrophilic or porous materials can be used. Color Reaction of Glutaraldehyde on nylon membrane with MBTH and FeCl 3 located on the same membrane. Cidex Glutaraldehyde Observation Color Green/blue Color develops in less than 1 min and stabilizes for more than 10 minutes.
  • the assay may be easily carried out on a nylon membrane.
  • Example 8 General Color Observation on Nylon Membrane with an Excess of MBTH and with MBTH and FeCl 3 Located on Two Separate Membranes.
  • an aldehyde tester 12 may be fabricated together on the membrane (Fig. 9B). Ideally this aldehyde tester could be separated from the main tester area 11 but close enough that diffusion of the aldehyde form the main tester area could reach the aldehyde tester region. This model will need only one single drop of the aldehyde solution. Schiff's reagent could be used for the test although other aldehyde reagents also could be used.
  • comparative color indicators may be integrated into the tester strip 14, 16.
  • the pH of the Cidex glutaraldehyde solution is related to the efficacy of glutaraldehyde.
  • the pH of the Cidex needs to be measured every time before use.
  • a pH tester 13 could be fabricated into a device so that no separate pH measurement is necessary ( Figures 9C-E).
  • the principle is the same as for the "aldehyde tester.”
  • a properly chosen pH dye could be used.
  • Single or mixture pH dyes could be used to effectively measure the pH range, usually in the pH 7-11 range.
  • Examples include but are not limited to bromothymol blue, brilliant yellow, neutral red, rosolic acid, phenol red, 3-nitrophenol, orange II, phenolphthalein, o -cresolphthalein, nile blue A and thymolphthalein etc.
  • a bar spectrum of different colors could be printed on the membrane chip or strip. The pH could be read directly by matching the color. In a preferred embodiment, the bar 15 should include pH 7-11.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Molecular Biology (AREA)
  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
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  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
EP02251865A 2001-03-16 2002-03-15 MBTH für die Messung von aliphatischen Aldehyden Ceased EP1248104A3 (de)

Applications Claiming Priority (2)

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US09/810,889 US7112448B2 (en) 2001-03-16 2001-03-16 MBTH for aliphatic aldehyde measurement
US810889 2001-03-16

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EP1248104A2 true EP1248104A2 (de) 2002-10-09
EP1248104A3 EP1248104A3 (de) 2003-01-15

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US (2) US7112448B2 (de)
EP (1) EP1248104A3 (de)
JP (1) JP2002328122A (de)
KR (1) KR20020073444A (de)
AU (1) AU2030702A (de)
CA (1) CA2376413A1 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102565043A (zh) * 2011-12-16 2012-07-11 邯郸派瑞电器有限公司 一种可快速检测空气中甲醛的试剂盒
CN109342419A (zh) * 2018-12-07 2019-02-15 云南商测质量检验技术服务有限公司 一种白酒中甲醇速测试剂及其使用方法

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7112448B2 (en) * 2001-03-16 2006-09-26 Ethicon, Inc. MBTH for aliphatic aldehyde measurement
JPWO2004111635A1 (ja) * 2003-06-12 2006-07-27 株式会社東洋発酵 アルデヒド検出用組成物
JP4769940B2 (ja) * 2006-02-20 2011-09-07 国立大学法人富山大学 ホルムアルデヒドの測定方法
JP4916003B2 (ja) * 2007-01-24 2012-04-11 独立行政法人産業技術総合研究所 アクロレイン及び／又はアクロレイン付加物を検出するための試薬及び方法
KR100903446B1 (ko) * 2007-10-25 2009-06-18 주식회사 동부하이텍 화학기계적 연마장치의 구리 검출방법
WO2016082003A1 (en) * 2014-11-26 2016-06-02 The University Of Melbourne Method and device for determination of aldehydes in biological samples

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EP0016578A1 (de) * 1979-03-10 1980-10-01 The British Petroleum Company p.l.c. Verfahren und Testsatz zur Bestimmung der Biozid-Konzentration in wässerigen Systemen
EP0769558A1 (de) * 1995-10-17 1997-04-23 Lifescan, Inc. Blutglucose-Teststreifen mit reduzierter Sensitivität für Hämatokrit

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Publication number Priority date Publication date Assignee Title
FR2198642A5 (en) * 1972-09-06 1974-03-29 Vogel Charles Uric acid assay in blood - using stable reagents containing uricase, catalase, methanol and colour formers
EP0016578A1 (de) * 1979-03-10 1980-10-01 The British Petroleum Company p.l.c. Verfahren und Testsatz zur Bestimmung der Biozid-Konzentration in wässerigen Systemen
EP0769558A1 (de) * 1995-10-17 1997-04-23 Lifescan, Inc. Blutglucose-Teststreifen mit reduzierter Sensitivität für Hämatokrit

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102565043A (zh) * 2011-12-16 2012-07-11 邯郸派瑞电器有限公司 一种可快速检测空气中甲醛的试剂盒
CN109342419A (zh) * 2018-12-07 2019-02-15 云南商测质量检验技术服务有限公司 一种白酒中甲醇速测试剂及其使用方法

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KR20020073444A (ko) 2002-09-26
US7112448B2 (en) 2006-09-26
AU2030702A (en) 2002-09-19
EP1248104A3 (de) 2003-01-15
US20060270052A1 (en) 2006-11-30
US20020168777A1 (en) 2002-11-14
CA2376413A1 (en) 2002-09-16
JP2002328122A (ja) 2002-11-15

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